


Double Trouble

by IceFemme



Category: Supernatural
Genre: Alternate Universe - High School, Alternate Universe - Student/Teacher, Anal Plug, Anal Sex, Bottom Jimmy, Come Shot, Dominant/Top Dean, Felching, Fingerfucking, M/M, Plot What Plot/Porn Without Plot, Rimming, Submissive/Bottom Castiel, Teacher Dean Winchester, Threesome - M/M/M, Twins
Language: English
Status: Completed
Published: 2013-06-23
Updated: 2013-06-23
Packaged: 2017-12-15 22:06:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,085
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/854531
Author URL: https://archiveofourown.org/users/IceFemme/pseuds/IceFemme
Summary: <blockquote class="userstuff">
              <p>Twins Jimmy and Castiel Novak play stupid to get their sexy professor Dean Winchester in bed with them.</p>
            </blockquote>





	Double Trouble

**Author's Note:**

> Big thank you to PoisonousDame for betaing at last minute!

“James and Castiel Novak?”

The man on the left glared at the teacher. “It’s _Jimmy_ ,” he seethed. Castiel slipped his hand from the tabletop to his brother’s lap to calm him down.

To his surprise, the teacher shot him an annoyed glare back. “Excuse me, but that’s what it says on this slip, you little fuck,” the teacher mumbled that last part under his breath. And it wasn’t just any teacher, but the student teacher that just graduated from a very important university on the west coast and very notorious for a bad attitude.

Nobody really knows that much about him—other than the fact that he’s a hothead sex-god with a serious exterior and a gorgeous face—his name is Dean Winchester.

_And_ he’s Castiel and Jimmy’s AP Biology student teacher for the semester.

“Doesn’t matter what your name is, kid; you’re failing,” Dean stated, crossing his arms over his chest. He looked in between the two twins. They were legitimately identical—no freckle or mole visible to tell them apart. In fact, their hair was styled the same way, they both wore similarly coloured tees and dark jeans, although the Jimmy one was wearing Vans that had a denim print and the other, Castiel, was wearing Hello Kitty designed slip on Vans. “And that is fucking me up, because I’m just a student teacher and it looks bad when all I have to do is teach for one semester and I already have two dinguses who don’t give a flying fuck.”

Both boys eyed him up and down. Jimmy decided he liked what he saw; he was already mapping out those sexy and plump lips, wondering where he could even start to explain how hot his professor was.

Castiel, on the other hand, really didn’t like being held up after school. Sure, the guy in front of him was gorgeous (fucking sex-god delivered from heaven), but he had better things to do. Better _people_ to do. There was hardly any fun in some tight-ass reprimanding dude who looked on the verge of giving him the ‘you’re better than this’ speech.

“Got anything to say? Either of you?” Dean demanded. “Look, I don’t want to have to talk to you about this either, but fuck—”

“You could… Come over tomorrow and tutor us,” Jimmy suggested quickly, cutting his teacher off. Castiel opened his mouth to protest but Jimmy slid closer to his twin brother and pinched his back.

Castiel sighed. It was worth a shot. “We… We could really use it,” he said, not liking the idea of actually admitting that to Dean. “Please.” He looked up and met his teacher’s eyes and for a moment Castiel thought he saw something click, something register because Dean furrowed his brow and sucked his lower lip into his mouth.

“Ye… Yeah. I can do that,” he said, his voice suddenly sounding tired and a lot calmer. “Where do you guys live?”

Jimmy eagerly gave the details while Castiel looked their teacher up and down. Maybe he would have a little fun with him. Maybe he would be surprised.

“We’re free all day,” Castiel added at the end, not missing the small, tiny—but definitely there—fleck of interest in Dean Winchester’s eyes.

* * *

 

Jimmy and Castiel were both wearing similar outfits again. But this time, since they were at home, Dean couldn’t check their shoes and tell the difference between them that way.

Castiel, with Dean’s understanding, was ten minutes older than Jimmy. With that said, Castiel directed Jimmy around—‘ _Make Dean a cup of coffee’_ , ‘ _What the hell are you doing on your ass; go get our homework out’_ , and ‘ _Stop staring, stupid, he’s right fucking here_ ’.

All Dean could think about was the fact that Jimmy is such a good little listener… funny how he somehow forgot how to do that in classes.

They sat down at a table in their room—which was a little odd to begin with. What two eighteen year olds would choose to share their room at this age, especially what with the fact that there are three other open bedrooms in the Novak’s large Private Drive house.

After about forty-five minutes in, Dean was starting to wonder why he was over here in the first place. The boys were smart in their own ways; they helped each other out and all but ignored Dean.

“So, do your parents ever mix you two up?” Dean started.

Castiel looked up with a smug smirk. Dean almost forgot how fucking hot he is—his slightly olive skin tone, shocking azure blue eyes, and that wild mess of black tresses. “You could say that.”

“Whenever they are here,” Jimmy commented under his breath as he leaned back in his chair.

His brother ignores him. “Do you even know which one of us is which right now?” Castiel asked, cocking an eyebrow up.

Dean chuckled because no, he really had no fucking clue. “Well,” he began; he glanced down at their papers. Their names were both scrawled at the top of their papers. Dean began to chuckle. “Castiel,” he pointed to the boy on the right, “Jimmy,” he pointed to the boy on the left.

They looked unimpressed. “I gave Jimmy my paper because he’s smarter and he can do his on his own later,” Castiel explained.

“You lose!” Jimmy declared. Both boys stood up eerily at the same exact moment.

Castiel’s lips curled up into a wicked grin. “We haven’t been completely honest with you, Mr. _Winchester_.”

“And I think that dishonest boys deserve to be punished,” Jimmy added, dropping to his knees before Dean and spreading the man’s worn jean clad knees apart.

“Hey—!” Dean began to struggle.

“We both have a pretty big crush on you,” Castiel explained. He feigned looking shy for a moment before leaning in and pressing his goddamn baby ass soft lips to Dean’s in a surprisingly chaste kiss. “And Jimmy’s a good little cockslut; if you give it to him he’ll do whatever you say, Dean,” he whispered softly against Dean’s lips.

Dean’s eyes met Jimmy’s briefly as the boy was pulling his zipper down with one of his canines. It was so undeniably sexy that Dean might have just gotten semi hard just now watching that. But Castiel had other plans. He jerked Dean’s chin towards him and pressed their lips together, this time much rougher.

The younger man slid his tongue into Dean’s mouth and cupped his jaw, refusing to allow his student teacher to move. Dean fights to try and dominate the kiss at that point—the point where he realizes that he wants this so bad too.

Like, seriously? Who doesn’t _dream_ of fucking twins?

Castiel’s lips moved fiercely against Dean’s and finally he parted the kiss, spit drooling out of the corner of Castiel’s mouth. He smirked again and slapped his little brother’s ass. Jimmy squealed because he had his hands wrapped firmly around Dean’s hardening cock and it caught him by surprise.

“Jimmy’s really excited, Dean. Can you tell?”

The older brother yanked Jimmy’s basketball shorts down past his ass and his cock comes out all dripping wet and hard. Castiel ran his hand down Jimmy’s back and then slid his fingers into the cleft of his ass and prodded the plug that was barely protruding from his wet hole.

Jimmy canted his ass and Dean could see the tip of the turquoise plug that’s already deep inside his ass. His breath hitched and his cock was ready to fucking go he’s so hard.

“Fuck yeah,” Dean grunted and got a nice grip on Castiel’s neck, surprising the usually arrogant and presumptuous boy (which makes Dean’s stomach coil in victory) and pulled him down to his knees beside his brother. “Your pussy wet too, baby? Getting hard off watching your little brother suck my cock?”

Castiel’s cheeks flared a pretty scarlet colour and Dean smirked. The older sibling bit his lower lip and nodded at his teacher. “Yes, sir,” he responded, dipping his head and licking at Dean’s slit which made him go absolutely wild—but he wouldn’t show the kid that.

“Why don’t you both suck my cock, huh?” And neither of them needed another pointer. Castiel swallowed Dean’s cock whole, sliding in almost all the way to his base until little tears formed in his eyes and he made a small choking sound. Dean gasped and held his head there for a little bit longer, enjoying the feel of the kid’s throat swallowing around him. “Oh, fuck yeah, Cas…”

No one commented on the name shortening but it only spurred the two boys to go even harder.

Castiel pulled back and licked his lips as Jimmy surged forward and licked up Dean’s length, his wide flat tongue curving underneath and touching a sensitive vein there which caused Dean to squeeze his eyes shut and groan. Castiel glared at his little brother for making Dean elicit such an approving noise and approached Dean’s cock.

Jimmy bobbed his head on the cockhead, licking around it and teasing the slit. Both boys enjoyed the encouraging, “Oh, fucking hell yeah, so fucking good to me… Never thought I’d be so lucky— _aauuh_ …!” He practically yipped when Cas’ hot mouth found Dean’s balls and sucked on them.

Both brothers took a side of Dean’s cock and stuck to their territory, licking and sucking and pretending not to notice when their tongues or lips met around the girth.

Jimmy glowered at his older brother and pushed forward and licked his tongue up around the cock, entering the mouth of his sibling. Castiel caught his eye and suddenly the cock was completely forgotten because both boys began going after each other’s mouths in frenzy.

Dean gasped in shock. It was one thing to share another guy’s dick with your brother, but to full on make out with him was a totally different ballpark in Dean’s opinion. Without any sense of restraint, Dean let out a string of curses in praise. He reached forward and carded his hand roughly though Castiel’s hair and yanked him up to his mouth, his cock’s taste now in his mouth along with his brother’s spit. It was fucking delicious.

Jimmy followed his brother and he leaned in to Dean’s neck and inhaled, planting kisses here and there.

“Alright Jimmy, I’m going to fuck you and I’m going to finger fuck your brother’s ass,” Dean growled at Jimmy who just gulped, his eyes turning dark and excited. He eagerly got off his knees and skipped to his bed to take a seat, waving for his older brother to join him.

“Don’t get your panties in a twist, Jimmy,” Castiel snarked, sitting down next to his brother and cupping his jaw to pull him in for a kiss. He shifted his little brother onto his lap and then lay back so that they were stacked on top of each other facing up, Jimmy’s back on Cas’ flat stomach so Jimmy had to crane his neck to meet his brother’s lips.

“I’m not wearing panties, Cassie,” Jimmy teased, sticking his tongue out at his sibling. Dean approached them and smirked.

“That’s how I fucking like it,” he breathed, spanking Jimmy’s ass. Dean crouched down so that the two asses were on his eye level, Castiel’s hard cock pushed out of the way so that Jimmy’s tailbone didn’t crush him.

Jimmy was giddy and loud like a second grader as Dean retracted the blue plug from his ass and brought it to his mouth for Jimmy to taste himself. Underneath him, Castiel opened his mouth eagerly for Dean to place the wet plug in his mouth as well.

“So sloppy and open for me, Jim,” Dean assessed, leaning in and licking a stripe up his perineum. “Don’t need to fuckin’ touch you and you’re already ready to go.”

“ _Deeean_!” Jimmy squealed. “In my ass—now _please_!”

Dean smirked, eyes connecting with Castiel who was placing comforting kisses on his little brother’s neck and shoulder.

“Because you asked so nicely,” Dean responded, reaching into the top drawer and (imagine that) there was a half full bottle of lube lying there. Dean generously coated his cock in lube and smeared it all over his fingers. Castiel gasped when he felt wet fingers prodding at his entrance, the tip of Dean’s index finger pushing in when his cockhead entered Jimmy’s hole.

Both brothers made their own noises of praise.

Dean thrust in and out quickly, teasing that little spot inside of Jimmy that made him buck back into Dean’s hips and try to get more. Dean just slapped his hands away whenever Jimmy tried to touch his cock, all the while fingering Castiel open harder, making the older brother groan loudly and shake under Jimmy.

“F—fuck, Dean!” Castiel cried.

“You’re so fucking sensitive, Cas,” Dean said, dipping forward and pressing his lips to Castiel’s. “So fucking cute. Just like your little brother.”

Dean slammed his cock all the way in and Jimmy gasped, feeling so delightfully full. He cried out and painted his belly with long streaks of white cum. Dean was so impressed of his student that he winked at him and smiled blindingly.

“Must be a little slut to be able to cum untouched, Jimmy,” he growled as he pulled out

His lips curled into a gallant smirk.

“My big brother taught me a thing or two,” he moaned elegantly, turning on his side so that he had a knee on either side of Castiel’s hips and had their lips firmly pressed together.

Dean growled and slapped Jimmy’s ass that was wriggling in his face. His cock was throbbing here and all the twins could do was tease him? That wasn’t very good hosting. If they had been at his place Dean knew he would take his time opening each little asshole up and lick them wide open…

“I think it’s time for Cassie to sit on my lap, don’t you think, _James_?”

Jimmy detached his face from his brother and glowered at Dean and pushed him over. “Sure thing, _Mr_. _Winchester_ ,” he returned. “If I can sit on your face so you eat my tight pussy out,” he added, pressing a slender finger to his lower lip with false coyness.

“Alright, baby,” Dean just smiled and spread his legs when Castiel suddenly wrapped his hand around Dean’s girth and sucked him into his mouth. “Ah, shit Cas! Just hop right fuckin’ on.”

Jimmy situated himself so that his semi hard cock was resting on Dean’s stubbly chin and his ass was promptly above his nose.

There was a brief pause in all movements as Jimmy was rubbing his ass-cunt over Dean’s lips and nose and Castiel was holding Dean’s cock right beneath his entrance. Then Dean’s tongue punctured the younger Novak’s ass while his dick fucked up into Cas.

Dean moaned loudly into Jimmy’s ass when Castiel’s sheer tightness struck Dean completely off guard. It was so fucking restricted that Dean saw white for a moment. And it occurred to him suddenly that he had hit the jackpot. He was fucking _twins_. _Identical_ _twins_. At the _same_ time.

He thrust up and Castiel whined low and lusty. He pushed his ass down and his little hole swallowed up Dean greedily.

“Oh, _Caaas_ … Mhmmm,” Dean moaned, pausing his lips against Jimmy’s swollen hole to catch his breath. Impatiently, Jimmy pushed back down and Dean growled, there was too much sensation going on and he was slowly losing it. He sucked hard on Jimmy’s rim when he finally noticed his orgasm was approaching faster than he had thought.

Jimmy outright laughed that was half excited and half condescending. “Are you going to cum?” Jimmy demanded, pushing his ass down and riding Dean’s wet tongue. “Are you going to fucking cum inside my brother? Gonna fucking blow after fucking both our slutty holes?”

Dean hummed in accord, squeezing his eyes shut tight and fucking up into Cas’ insatiable ass. “Fuck _yeah_ , Jimmy. Fucking Cas, aaahh,” he groaned, clenching his teeth as he sucked on Jimmy’s rim. Something remotely occurred to him that he “ _Shouldn’t be fucking doing this_!!” And he shouldn’t. Oh well.

Cas purposefully clenched down on Dean as he rode the thick cock inside of him, causing Dean to snarl and fuck up harshly into Cas. Jimmy got off his face and turned around to push his throbbing cock into Dean’s mouth. Dean sucked ferociously as he fucked, his voice choked thanks to the member fucking into his face.

His orgasm ripped through him and he came heavily into the older twin. “Holy fucking shit!” Cas absolutely shrieked. Jimmy’s moans were higher and he fucked into Dean’s mouth harshly. One last cry and he was cumming buckets into his professor’s face.

Castiel hopped off Dean’s cock and kneeled on the other side of Dean’s head, the older man’s hand came up and wrapped around his girth and began to stroke him, his other hand rubbing the last of Jimmy’s cum out of him. Cas’s own orgasm came with a high cry and reached forward to turn Dean’s sweaty and cum streaked face towards his cock as he blew all over his face.

There was no speaking for what felt like a half hour, but was probably anywhere from three to eight minutes. So when Castiel spoke, Dean was shocked that he could still hear. “You’re so fucking sexy, Professor,” Cas groaned, rubbing his slowly softening cock over Dean’s swollen pink lips.

“You gonna give us that A, Sir?” Jimmy asked.

“We won’t be naughty students anymore,” Castiel promised. There was too much attention on Dean in that moment and he scoffed.

“I mean, I guess we could work something out, you know, if there are more consecutive study sessions, you two should be able to get your grades up,” Dean spoke easily, a smirk sliding onto his face.

If anyone were to walk into the room at that moment (the twin’s parents, god forbid, they were so fucking loud) and heard Dean say that, they would think he was genuinely telling them some valid information.

“We have lacrosse twice a week, so how about Monday, Wednesday, Friday?” Jimmy asked with a sly smirk.

“We’re very behind!” Castiel encouraged and Dean caved. He swiped a finger across his cheek and collected the mixture of the twin’s cum and brought it into his mouth, sucking on the two digits and smiling deviously.

“That can be arranged.”


End file.
